Reaction #4530

Reaction equation

p-nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-3-acetylthio-3-(2-ethoxyethylthio)-acrylate

m-chloroperbenzoic acid

→

p-Nitrobenzyl 2-(4-ethylsulfinyl-2-oxo-1-azetidinyl)-3-acetylthio-3-(2-ethoxyethylthio)acrylate

Solvents

methylene chloride

methylene chloride

Conditions

Workup

1. 1
   WashThe methylene chloride solution was then washed with two 25 ml portions of saturated aqueous sodium bicarbonate solution and two 25 ml portions of water
2. 2
   Dryingdried over anhydrous sodium sulfate
3. 3
   Concentrationconcentrated in vacuo to an oil
4. 4
   OtherThe crude title compound (1.25 g) was used without further purification
5. 5
   Otherabsorption bands at 5.6 and 5.79 microns

Procedure

A solution of 1.4 g p-nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-3-acetylthio-3-(2-ethoxyethylthio)-acrylate in 75 ml. methylene chloride was cooled to 0° C. under a nitrogen atmosphere. A solution of 0.551 g m-chloroperbenzoic acid in 25 ml methylene chloride was added dropwise, then the reaction mixture was stirred at 0° C. for 1 hour. The methylene chloride solution was then washed with two 25 ml portions of saturated aqueous sodium bicarbonate solution and two 25 ml portions of water, dried over anhydrous sodium sulfate and concentrated in vacuo to an oil. The crude title compound (1.25 g) was used without further purification. The NMR spectrum of a deuterochloroform solution showed peaks at 1.24(m, 6H); 2.27-3.74(c, 13H); 4.7-5.46 (c, 3H); 7.57(m, 2H); and 8.23(m, 2H) ppm. The infrared spectrum of a dichloromethane solution has absorption bands at 5.6 and 5.79 microns.

Source